DE4404183A1 - 4-Amino-1-piperidylbenzoylguanidine - Google Patents

4-Amino-1-piperidylbenzoylguanidine

Info

Publication number: DE4404183A1
Authority: DE; Germany
Prior art keywords: diaminomethylene; formula; piperidino; boc; methylsulfonyl
Prior art date: 1994-02-10
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

DE4404183A

Other languages

German (de)

English (en)

Inventor

Rolf Dr Gericke

Manfred Dr Baumgarth

Dieter Dr Dorsch

Norbert Dr Beier

Klaus Otto Dr Minck

Inge Dr Lues

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Merck Patent GmbH

Original Assignee

Merck Patent GmbH

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1994-02-10

Filing date

1994-02-10

Publication date

1995-08-17

1994-02-10 Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH

1994-02-10 Priority to DE4404183A priority Critical patent/DE4404183A1/de

1995-02-06 Priority to AU11571/95A priority patent/AU693496B2/en

1995-02-07 Priority to EP95101575A priority patent/EP0667341B1/fr

1995-02-07 Priority to SK157-95A priority patent/SK281721B6/sk

1995-02-07 Priority to TW084100981A priority patent/TW291476B/zh

1995-02-07 Priority to AT95101575T priority patent/ATE204864T1/de

1995-02-07 Priority to DE59509543T priority patent/DE59509543D1/de

1995-02-07 Priority to PT95101575T priority patent/PT667341E/pt

1995-02-07 Priority to DK95101575T priority patent/DK0667341T3/da

1995-02-07 Priority to ES95101575T priority patent/ES2161789T3/es

1995-02-07 Priority to CN95101910A priority patent/CN1082948C/zh

1995-02-08 Priority to CA002142070A priority patent/CA2142070A1/fr

1995-02-08 Priority to UA95028120A priority patent/UA43834C2/uk

1995-02-08 Priority to CZ1995327A priority patent/CZ286681B6/cs

1995-02-09 Priority to ZA951059A priority patent/ZA951059B/xx

1995-02-09 Priority to US08/385,790 priority patent/US5461066A/en

1995-02-09 Priority to PL95307190A priority patent/PL179255B1/pl

1995-02-09 Priority to RU95101843A priority patent/RU2140412C1/ru

1995-02-09 Priority to NO950485A priority patent/NO303685B1/no

1995-02-09 Priority to KR1019950002288A priority patent/KR950321212A/ko

1995-02-09 Priority to HU9500396A priority patent/HU215601B/hu

1995-02-10 Priority to JP7022475A priority patent/JPH07267926A/ja

1995-08-17 Publication of DE4404183A1 publication Critical patent/DE4404183A1/de

2001-10-09 Priority to GR20010401701T priority patent/GR3036839T3/el

Status Withdrawn legal-status Critical Current

Links

BEDVALDDNUBBNZ-UHFFFAOYSA-N n-(4-aminopiperidin-1-yl)-n-carbamimidoylbenzamide Chemical compound C1CC(N)CCN1N(C(N)=N)C(=O)C1=CC=CC=C1 BEDVALDDNUBBNZ-UHFFFAOYSA-N 0.000 title claims abstract description 5
-1 tetrahydroquinolyl Chemical group 0.000 claims abstract description 94
150000003839 salts Chemical class 0.000 claims abstract description 18
125000002947 alkylene group Chemical group 0.000 claims abstract description 12
229910052801 chlorine Inorganic materials 0.000 claims abstract description 10
229910052794 bromium Inorganic materials 0.000 claims abstract description 8
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
229910052740 iodine Inorganic materials 0.000 claims abstract description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 4
125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims abstract description 3
229910052731 fluorine Inorganic materials 0.000 claims abstract description 3
125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 3
125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 34
150000001875 compounds Chemical class 0.000 claims description 31
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 19
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 15
238000011282 treatment Methods 0.000 claims description 11
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
238000002360 preparation method Methods 0.000 claims description 9
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
150000003053 piperidines Chemical class 0.000 claims description 5
206010061216 Infarction Diseases 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 4
230000007574 infarction Effects 0.000 claims description 4
239000007788 liquid Substances 0.000 claims description 4
239000000825 pharmaceutical preparation Substances 0.000 claims description 4
230000003449 preventive effect Effects 0.000 claims description 4
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 4
206010002383 Angina Pectoris Diseases 0.000 claims description 3
206010003119 arrhythmia Diseases 0.000 claims description 3
230000006793 arrhythmia Effects 0.000 claims description 3
229940079593 drug Drugs 0.000 claims description 3
AJDQRQQNNLZLPM-UHFFFAOYSA-N n-(diaminomethylidene)benzamide Chemical compound NC(N)=NC(=O)C1=CC=CC=C1 AJDQRQQNNLZLPM-UHFFFAOYSA-N 0.000 claims description 3
108090000765 processed proteins & peptides Proteins 0.000 claims description 3
125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 3
125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
JMBURABQFHCZKT-UHFFFAOYSA-N n-(diaminomethylidene)-4-[4-(3-methyl-2-oxobenzimidazol-1-yl)piperidin-1-yl]-3-methylsulfonylbenzamide Chemical compound O=C1N(C)C2=CC=CC=C2N1C(CC1)CCN1C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O JMBURABQFHCZKT-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
QXVOVDGWQHWZJF-UHFFFAOYSA-N tert-butyl n-[1-[4-(diaminomethylidenecarbamoyl)-2-methylsulfonylphenyl]piperidin-4-yl]carbamate Chemical compound C1CC(NC(=O)OC(C)(C)C)CCN1C1=CC=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O QXVOVDGWQHWZJF-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 abstract description 5
125000000623 heterocyclic group Chemical group 0.000 abstract description 2
125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 abstract 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
238000006243 chemical reaction Methods 0.000 description 24
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000004480 active ingredient Substances 0.000 description 16
KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 13
239000000126 substance Substances 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000002585 base Substances 0.000 description 11
239000000243 solution Substances 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
239000002904 solvent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
239000000203 mixture Substances 0.000 description 8
239000000460 chlorine Substances 0.000 description 7
150000003254 radicals Chemical class 0.000 description 7
239000003826 tablet Substances 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000000155 melt Substances 0.000 description 5
210000000056 organ Anatomy 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
241000282414 Homo sapiens Species 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
125000002252 acyl group Chemical group 0.000 description 4
235000019253 formic acid Nutrition 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
239000005711 Benzoic acid Substances 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
230000010933 acylation Effects 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
230000003288 anthiarrhythmic effect Effects 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
239000002775 capsule Substances 0.000 description 3
150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000012154 double-distilled water Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000011521 glass Substances 0.000 description 3
PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
125000003386 piperidinyl group Chemical group 0.000 description 3
239000000047 product Substances 0.000 description 3
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000829 suppository Substances 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
CKXZPVPIDOJLLM-UHFFFAOYSA-N tert-butyl n-piperidin-4-ylcarbamate Chemical compound CC(C)(C)OC(=O)NC1CCNCC1 CKXZPVPIDOJLLM-UHFFFAOYSA-N 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
238000002560 therapeutic procedure Methods 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
238000010626 work up procedure Methods 0.000 description 3
VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 description 3
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 2
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 2
ZWBQTUAUWSDCKX-UHFFFAOYSA-N 4-chloro-3-methylsulfonylbenzoic acid Chemical compound CS(=O)(=O)C1=CC(C(O)=O)=CC=C1Cl ZWBQTUAUWSDCKX-UHFFFAOYSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
102000003669 Antiporters Human genes 0.000 description 2
108090000084 Antiporters Proteins 0.000 description 2
206010003210 Arteriosclerosis Diseases 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000282472 Canis lupus familiaris Species 0.000 description 2
241000282693 Cercopithecidae Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
208000002249 Diabetes Complications Diseases 0.000 description 2
206010012655 Diabetic complications Diseases 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
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GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
241000699670 Mus sp. Species 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
206010028980 Neoplasm Diseases 0.000 description 2
PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
241000700159 Rattus Species 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
239000002168 alkylating agent Substances 0.000 description 2
229940100198 alkylating agent Drugs 0.000 description 2
230000029936 alkylation Effects 0.000 description 2
238000005804 alkylation reaction Methods 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
150000008064 anhydrides Chemical class 0.000 description 2
239000003416 antiarrhythmic agent Substances 0.000 description 2
208000011775 arteriosclerosis disease Diseases 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
230000037396 body weight Effects 0.000 description 2
150000001735 carboxylic acids Chemical class 0.000 description 2
230000004663 cell proliferation Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 2
230000000694 effects Effects 0.000 description 2
230000032050 esterification Effects 0.000 description 2
238000005886 esterification reaction Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
125000005843 halogen group Chemical group 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
206010020718 hyperplasia Diseases 0.000 description 2
230000001146 hypoxic effect Effects 0.000 description 2
238000009413 insulation Methods 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
208000028867 ischemia Diseases 0.000 description 2
230000000302 ischemic effect Effects 0.000 description 2
SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
210000004072 lung Anatomy 0.000 description 2
235000019359 magnesium stearate Nutrition 0.000 description 2
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
YUVSGFLZOSEKEA-UHFFFAOYSA-N methyl 4-fluoro-3-methylsulfonylbenzoate Chemical compound COC(=O)C1=CC=C(F)C(S(C)(=O)=O)=C1 YUVSGFLZOSEKEA-UHFFFAOYSA-N 0.000 description 2
210000000653 nervous system Anatomy 0.000 description 2
238000006396 nitration reaction Methods 0.000 description 2
229910017604 nitric acid Inorganic materials 0.000 description 2
150000002825 nitriles Chemical class 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
239000002674 ointment Substances 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000001301 oxygen Substances 0.000 description 2
235000019271 petrolatum Nutrition 0.000 description 2
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 2
235000011007 phosphoric acid Nutrition 0.000 description 2
WLJVNTCWHIRURA-UHFFFAOYSA-N pimelic acid Chemical compound OC(=O)CCCCCC(O)=O WLJVNTCWHIRURA-UHFFFAOYSA-N 0.000 description 2
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QWCBOLPNMBTPTQ-UHFFFAOYSA-N tert-butyl 2-amino-1-[2-chloro-4-(diaminomethylidenecarbamoyl)-6-methylsulfonylphenyl]piperidine-4-carboxylate Chemical compound NC1CC(C(=O)OC(C)(C)C)CCN1C1=C(Cl)C=C(C(=O)N=C(N)N)C=C1S(C)(=O)=O QWCBOLPNMBTPTQ-UHFFFAOYSA-N 0.000 description 1
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BYCFGQDGEIXLCH-UHFFFAOYSA-N tert-butyl 2-amino-1-[5-(diaminomethylidenecarbamoyl)-2-methylsulfonylphenyl]piperidine-4-carboxylate Chemical compound NC1CC(C(=O)OC(C)(C)C)CCN1C1=CC(C(=O)N=C(N)N)=CC=C1S(C)(=O)=O BYCFGQDGEIXLCH-UHFFFAOYSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Chemical Kinetics & Catalysis (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

DE4404183A 1994-02-10 1994-02-10 4-Amino-1-piperidylbenzoylguanidine Withdrawn DE4404183A1 (de)

Priority Applications (23)

Application Number	Priority Date	Filing Date	Title
DE4404183A DE4404183A1 (de)	1994-02-10	1994-02-10	4-Amino-1-piperidylbenzoylguanidine
AU11571/95A AU693496B2 (en)	1994-02-10	1995-02-06	4-amino-1-piperidylbenzoylguanidine
EP95101575A EP0667341B1 (fr)	1994-02-10	1995-02-07	4-Amino-1-pipéridylbenzoyl guanidines comme inhibiteurs Na+/H+ antiporter
SK157-95A SK281721B6 (sk)	1994-02-10	1995-02-07	N-diaminometylén-4-(4-aminopiperidino)-5- metylsulfonylbenzamidové deriváty, ich použitie na výrobu liečiv a farmaceutické prostriedky na ich báze
TW084100981A TW291476B (fr)	1994-02-10	1995-02-07
AT95101575T ATE204864T1 (de)	1994-02-10	1995-02-07	4-amino-1-piperidylbenzoylguanidine als na+/h+- antiporter inhibitoren
DE59509543T DE59509543D1 (de)	1994-02-10	1995-02-07	4-Amino-1-piperidylbenzoylguanidine als Na+/H+-antiporter Inhibitoren
PT95101575T PT667341E (pt)	1994-02-10	1995-02-07	4-amino-1-peperidilbenzoilguanidinas como inibidores do antiporte na+/h+
DK95101575T DK0667341T3 (da)	1994-02-10	1995-02-07	4-Amino-1-piperidylbenzoylguanidiner som Na+/H+-antiporter-inhibitorer
ES95101575T ES2161789T3 (es)	1994-02-10	1995-02-07	4-amino-1-piperidilbenzoilguanidinas.
CN95101910A CN1082948C (zh)	1994-02-10	1995-02-07	4－氨基－1－哌啶基苯甲酰基胍
CA002142070A CA2142070A1 (fr)	1994-02-10	1995-02-08	4-amino-1-piperidylbenzoylguanidines
UA95028120A UA43834C2 (uk)	1994-02-10	1995-02-08	4-аміно-1-піперидилбензоїлгуанідини, спосіб їх одержання (варіанти), фармацевтична композиція на їх основі та спосіб її одержання
CZ1995327A CZ286681B6 (en)	1994-02-10	1995-02-08	N-diaminomethylene-4-(4-aminopiperidino)-5-methylsulfonylbenzamide derivatives, their use for preparing medicaments and pharmaceutical preparation based thereon
NO950485A NO303685B1 (no)	1994-02-10	1995-02-09	4-amino-1-piperidylbenzoylguanidiner, farmasøytiske preparater som inneholder et slikt, og anvendelse av slike forbindelser til fremstilling av et legemiddel
US08/385,790 US5461066A (en)	1994-02-10	1995-02-09	4-amino-1-piperidylbenzoylguanidines
PL95307190A PL179255B1 (pl)	1994-02-10	1995-02-09	N owe pochodne 4-aminopiperydylo-(1 )-benzoiloguanidyny, sposób ich wytwarzania oraz preparat farmaceutyczny PL PL PL PL PL PL PL
RU95101843A RU2140412C1 (ru)	1994-02-10	1995-02-09	4-амино-1-пиперидилбензоилгуанидины или их физиологически приемлемые соли, способы их получения, фармацевтическая композиция и способ ее получения
ZA951059A ZA951059B (en)	1994-02-10	1995-02-09	4-amino-1-piperidylbenzoylguanidine
KR1019950002288A KR950321212A (ko)	1994-02-10	1995-02-09	4-아미노-1-피페리딜벤조일구아니딘
HU9500396A HU215601B (hu)	1994-02-10	1995-02-09	4-Amino-1-piperidil-benzoil-guanidin-származékok, ezeket tartalmazó gyógyászati készítmények, eljárás ezek előállítására, és alkalmazásuk gyógyszerkészítmények előállítására
JP7022475A JPH07267926A (ja)	1994-02-10	1995-02-10	４−アミノ−１−ピペリジルベンゾイルグアニジン
GR20010401701T GR3036839T3 (en)	1994-02-10	2001-10-09	4-Amino-1-piperidylbenzoylguanidines as Na+/H+ antiporter inhibitors.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE4404183A DE4404183A1 (de)	1994-02-10	1994-02-10	4-Amino-1-piperidylbenzoylguanidine

Publications (1)

Publication Number	Publication Date
DE4404183A1 true DE4404183A1 (de)	1995-08-17

Family

ID=6509922

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
DE4404183A Withdrawn DE4404183A1 (de)	1994-02-10	1994-02-10	4-Amino-1-piperidylbenzoylguanidine
DE59509543T Expired - Fee Related DE59509543D1 (de)	1994-02-10	1995-02-07	4-Amino-1-piperidylbenzoylguanidine als Na+/H+-antiporter Inhibitoren

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
DE59509543T Expired - Fee Related DE59509543D1 (de)	1994-02-10	1995-02-07	4-Amino-1-piperidylbenzoylguanidine als Na+/H+-antiporter Inhibitoren

Country Status (22)

Country	Link
US (1)	US5461066A (fr)
EP (1)	EP0667341B1 (fr)
JP (1)	JPH07267926A (fr)
KR (1)	KR950321212A (fr)
CN (1)	CN1082948C (fr)
AT (1)	ATE204864T1 (fr)
AU (1)	AU693496B2 (fr)
CA (1)	CA2142070A1 (fr)
CZ (1)	CZ286681B6 (fr)
DE (2)	DE4404183A1 (fr)
DK (1)	DK0667341T3 (fr)
ES (1)	ES2161789T3 (fr)
GR (1)	GR3036839T3 (fr)
HU (1)	HU215601B (fr)
NO (1)	NO303685B1 (fr)
PL (1)	PL179255B1 (fr)
PT (1)	PT667341E (fr)
RU (1)	RU2140412C1 (fr)
SK (1)	SK281721B6 (fr)
TW (1)	TW291476B (fr)
UA (1)	UA43834C2 (fr)
ZA (1)	ZA951059B (fr)

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DE19608162A1 (de) *	1996-03-04	1997-09-11	Hoechst Ag	Ortho-substituierte Benzoylguanidine, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
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US20050261278A1 (en)	2004-05-21	2005-11-24	Weiner David M	Selective serotonin receptor inverse agonists as therapeutics for disease
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BRPI0515015A (pt) *	2004-08-11	2008-07-01	Kyorin Seiyaku Kk	derivado cìclico de ácido aminobenzóico; medicamento; agonista ppar(alpha); agonista duplo ppar(alpha), y; agonista duplo ppar(alpha), (delta); modulador ppar; agente lipìdeo; agente profilático ou terapêutico compreendendo pelo menos um dos derivados cìclicos de ácido aminobenzóico ou sal do mesmo farmacêuticamente aceitável
US7790899B2 (en) *	2004-09-27	2010-09-07	Acadia Pharmaceuticals, Inc.	Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms
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DE102004054054A1 (de)	2004-11-05	2006-05-11	Boehringer Ingelheim Pharma Gmbh & Co. Kg	Verfahren zur Herstellung chiraler 8-(3-Amino-piperidin-1-yl)-xanthine
EP1852108A1 (fr)	2006-05-04	2007-11-07	Boehringer Ingelheim Pharma GmbH & Co.KG	Compositions d'inhibiteurs de la DPP IV
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PE20080251A1 (es)	2006-05-04	2008-04-25	Boehringer Ingelheim Int	Usos de inhibidores de dpp iv
EP2134330B1 (fr)	2007-03-19	2013-05-08	Acadia Pharmaceuticals Inc.	Combinaisons d'agonistes inverses ou antagonistes de 5-ht2a avec antipsychotiques
CA2700331A1 (fr) *	2007-09-21	2009-03-26	Acadia Pharmaceuticals, Inc.	Co-administration de pimavanserine avec d'autres agents
PE20091730A1 (es)	2008-04-03	2009-12-10	Boehringer Ingelheim Int	Formulaciones que comprenden un inhibidor de dpp4
BRPI0916997A2 (pt)	2008-08-06	2020-12-15	Boehringer Ingelheim International Gmbh	Inibidor de dpp-4 e seu uso
US20200155558A1 (en)	2018-11-20	2020-05-21	Boehringer Ingelheim International Gmbh	Treatment for diabetes in patients with insufficient glycemic control despite therapy with an oral antidiabetic drug
EP2382216A1 (fr)	2008-12-23	2011-11-02	Boehringer Ingelheim International GmbH	Formes de sel d'un composé organique
EP3646859A1 (fr)	2009-11-27	2020-05-06	Boehringer Ingelheim International GmbH	Traitement de patients diabétiques génotypés avec des inhibiteurs de dpp-iv tels que la linagliptine
AU2011249722B2 (en)	2010-05-05	2015-09-17	Boehringer Ingelheim International Gmbh	Combination therapy
CN106975074A (zh)	2010-06-24	2017-07-25	勃林格殷格翰国际有限公司	糖尿病治疗
AR083878A1 (es)	2010-11-15	2013-03-27	Boehringer Ingelheim Int	Terapia antidiabetica vasoprotectora y cardioprotectora, linagliptina, metodo de tratamiento
PH12014500137A1 (en)	2011-07-15	2017-08-18	Boehringer Ingelheim Int	Substituted quinazolines, the preparation thereof and the use thereof in pharmaceutical compositions
US9555001B2 (en)	2012-03-07	2017-01-31	Boehringer Ingelheim International Gmbh	Pharmaceutical composition and uses thereof
WO2013171167A1 (fr)	2012-05-14	2013-11-21	Boehringer Ingelheim International Gmbh	Dérivé de xanthine en tant qu'inhibiteur de dpp-4 pour l'utilisation dans le traitement de troubles associés aux podocytes et/ou un syndrome néphrotique
US20130303554A1 (en)	2012-05-14	2013-11-14	Boehringer Ingelheim International Gmbh	Use of a dpp-4 inhibitor in sirs and/or sepsis
WO2013174767A1 (fr)	2012-05-24	2013-11-28	Boehringer Ingelheim International Gmbh	Dérivé de xanthine en tant qu'inhibiteur de la dpp-4 à utiliser dans la modification de l'apport alimentaire et dans la régulation des préférences alimentaires
EP3110449B1 (fr)	2014-02-28	2023-06-28	Boehringer Ingelheim International GmbH	Utilisation médicale d'un inhibiteur de dpp-4
EP3325444B1 (fr)	2015-07-20	2021-07-07	Acadia Pharmaceuticals Inc.	Procédé de préparation de n-(4-fluorobenzyl)-n-(1-méthylpipéridin-4-yl)-n'-(4-(2-méthylpropyloxy) phénylméthyl)carbamide et son sel de tartrate et forme polymorphe c
US10953000B2 (en)	2016-03-25	2021-03-23	Acadia Pharmaceuticals Inc.	Combination of pimavanserin and cytochrome P450 modulators
WO2017165635A1 (fr)	2016-03-25	2017-09-28	Acadia Pharmaceuticals Inc.	Association de pimavansérine et de modulateurs du cytochrome p450
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1994
- 1994-02-10 DE DE4404183A patent/DE4404183A1/de not_active Withdrawn
1995
- 1995-02-06 AU AU11571/95A patent/AU693496B2/en not_active Ceased
- 1995-02-07 SK SK157-95A patent/SK281721B6/sk unknown
- 1995-02-07 TW TW084100981A patent/TW291476B/zh active
- 1995-02-07 AT AT95101575T patent/ATE204864T1/de not_active IP Right Cessation
- 1995-02-07 EP EP95101575A patent/EP0667341B1/fr not_active Expired - Lifetime
- 1995-02-07 DK DK95101575T patent/DK0667341T3/da active
- 1995-02-07 ES ES95101575T patent/ES2161789T3/es not_active Expired - Lifetime
- 1995-02-07 DE DE59509543T patent/DE59509543D1/de not_active Expired - Fee Related
- 1995-02-07 CN CN95101910A patent/CN1082948C/zh not_active Expired - Fee Related
- 1995-02-07 PT PT95101575T patent/PT667341E/pt unknown
- 1995-02-08 CZ CZ1995327A patent/CZ286681B6/cs not_active IP Right Cessation
- 1995-02-08 UA UA95028120A patent/UA43834C2/uk unknown
- 1995-02-08 CA CA002142070A patent/CA2142070A1/fr not_active Abandoned
- 1995-02-09 PL PL95307190A patent/PL179255B1/pl unknown
- 1995-02-09 RU RU95101843A patent/RU2140412C1/ru active
- 1995-02-09 US US08/385,790 patent/US5461066A/en not_active Expired - Fee Related
- 1995-02-09 NO NO950485A patent/NO303685B1/no not_active IP Right Cessation
- 1995-02-09 KR KR1019950002288A patent/KR950321212A/ko not_active Abandoned
- 1995-02-09 ZA ZA951059A patent/ZA951059B/xx unknown
- 1995-02-09 HU HU9500396A patent/HU215601B/hu not_active IP Right Cessation
- 1995-02-10 JP JP7022475A patent/JPH07267926A/ja active Pending
2001
- 2001-10-09 GR GR20010401701T patent/GR3036839T3/el not_active IP Right Cessation

Also Published As

Publication number	Publication date
RU95101843A (ru)	1997-03-10
NO303685B1 (no)	1998-08-17
TW291476B (fr)	1996-11-21
AU693496B2 (en)	1998-07-02
HU9500396D0 (en)	1995-03-28
CZ286681B6 (en)	2000-06-14
HU215601B (hu)	1999-01-28
NO950485D0 (no)	1995-02-09
RU2140412C1 (ru)	1999-10-27
UA43834C2 (uk)	2002-01-15
ZA951059B (en)	1995-10-13
CN1082948C (zh)	2002-04-17
DE59509543D1 (de)	2001-10-04
NO950485L (no)	1995-08-11
PL307190A1 (en)	1995-08-21
SK281721B6 (sk)	2001-07-10
ES2161789T3 (es)	2001-12-16
DK0667341T3 (da)	2001-10-22
PL179255B1 (pl)	2000-08-31
CZ32795A3 (en)	1995-10-18
SK15795A3 (en)	1995-09-13
KR950321212A (ko)	1995-12-20
PT667341E (pt)	2001-12-28
HUT72306A (en)	1996-04-29
CN1112550A (zh)	1995-11-29
JPH07267926A (ja)	1995-10-17
EP0667341B1 (fr)	2001-08-29
ATE204864T1 (de)	2001-09-15
US5461066A (en)	1995-10-24
CA2142070A1 (fr)	1995-08-11
AU1157195A (en)	1995-08-17
EP0667341A1 (fr)	1995-08-16
GR3036839T3 (en)	2002-01-31

Publication	Publication Date	Title
DE4404183A1 (de)	1995-08-17	4-Amino-1-piperidylbenzoylguanidine
EP0699666B1 (fr)	1999-01-07	Hétérocyclyl-benzoylguanidines.
EP0556674B1 (fr)	1996-06-19	Benzoylguanidines 3,5-substitués avec une activité antiarrhythmique et une activité inhibitrice de la prolifération des cellules
EP0416499B1 (fr)	1995-04-26	Benzoylguanidines, procédé pour leur préparation, leur utilisation comme médicaments ainsi que médicaments les contenant
EP0589336A1 (fr)	1994-03-30	Benzoylguanidines, leur procédé de préparation et leur utilisation comme agents antiarrhythmiques
WO2001087829A1 (fr)	2001-11-22	Bisacylguanidine
EP0758644B1 (fr)	2003-10-15	Dérivés de sulfonyl- ou sulfinyl-benzoyl-guanidine
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